WO2017022982A1 - Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et dispositif électronique comprenant celui-ci - Google Patents

Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et dispositif électronique comprenant celui-ci Download PDF

Info

Publication number
WO2017022982A1
WO2017022982A1 PCT/KR2016/007862 KR2016007862W WO2017022982A1 WO 2017022982 A1 WO2017022982 A1 WO 2017022982A1 KR 2016007862 W KR2016007862 W KR 2016007862W WO 2017022982 A1 WO2017022982 A1 WO 2017022982A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
formula
compound
ring
organic
Prior art date
Application number
PCT/KR2016/007862
Other languages
English (en)
Korean (ko)
Inventor
김원삼
이선희
박정근
정화순
변지훈
박보람
강문성
박정환
김석현
Original Assignee
덕산네오룩스 주식회사
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 덕산네오룩스 주식회사 filed Critical 덕산네오룩스 주식회사
Publication of WO2017022982A1 publication Critical patent/WO2017022982A1/fr

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using organic materials.
  • An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • Materials used as the organic material layer in the organic electric device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their functions.
  • the light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. Can be.
  • the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural colors according to light emitting colors.
  • the maximum light emission wavelength is shifted to the long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the light emission attenuation.
  • the host / dopant system can be used as the light emitting material.
  • the principle is that when a small amount of dopant having a smaller energy band gap than the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant to produce high-efficiency light.
  • the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
  • Efficiency, lifespan, and driving voltage are related to each other, and as the efficiency increases, the driving voltage decreases relatively, and the crystallization of organic materials due to Joule heating generated during driving decreases as the driving voltage decreases.
  • the lifespan tends to increase.
  • simply improving the organic material layer does not maximize the efficiency. This is because a long life and high efficiency can be achieved at the same time when an optimal combination of energy level and T1 value and intrinsic properties (mobility, interfacial properties, etc.) of each organic material layer is achieved. Therefore, there is a need for the development of a light emitting material having high thermal stability and efficiently achieving a charge balance in the light emitting layer.
  • materials constituting the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and a light emitting auxiliary layer material, are stable and efficient. Supported by the material should be preceded, but development of a stable and efficient organic material layer for an organic electric device has not been made yet. Therefore, the development of new materials is continuously required, and in particular, the development of the host material of the light emitting layer is urgently required.
  • Patent Document 1 US6596415 B2
  • Patent Document 2 US6465115 B2
  • An object of the present invention is to provide a compound capable of improving high luminous efficiency, low driving voltage, high heat resistance, color purity, and lifetime of an element, an organic electric element using the same, and an electronic device thereof.
  • the present invention provides a compound represented by the following formula.
  • the present invention provides an organic electronic device using the compound represented by the above formula and an electronic device thereof.
  • FIG. 1 is an exemplary view of an organic electroluminescent device according to the present invention.
  • first, second, A, B, (a), and (b) can be used. These terms are only for distinguishing the components from other components, and the nature, order or order of the components are not limited by the terms. If a component is described as being “connected”, “coupled” or “connected” to another component, that component may be directly connected to or connected to that other component, but there may be another configuration between each component. It is to be understood that the elements may be “connected”, “coupled” or “connected”. In addition, if a component such as a layer, film, region, plate, etc. is said to be “on” or “on” another component, it is not only when the other component is “right on” but also another component in between. It is to be understood that this may also include cases. On the contrary, when a component is said to be “directly above” another part, it should be understood to mean that there is no other part in the middle.
  • halo or halogen as used herein is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I) unless otherwise indicated.
  • alkyl or “alkyl group” has a single bond of 1 to 60 carbon atoms, unless otherwise indicated, and is a straight chain alkyl group, branched chain alkyl group, cycloalkyl (alicyclic) group, alkyl-substituted cyclo Radicals of saturated aliphatic functional groups, including alkyl groups, cycloalkyl-substituted alkyl groups.
  • alkenyl group or “alkynyl group”, unless stated otherwise, has a double or triple bond of 2 to 60 carbon atoms, and includes a straight or branched chain group, and is not limited thereto. It is not.
  • cycloalkyl refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.
  • alkoxy group or "alkyloxy group” means an alkyl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 1 to 60, but is not limited thereto.
  • aryloxyl group or “aryloxy group” means an aryl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 6 to 60, but is not limited thereto.
  • fluorenyl group or “fluorenylene group” means a monovalent or divalent functional group in which R, R 'and R “are all hydrogen in the following structures, unless otherwise stated, and" Substituted fluorenyl group “or” substituted fluorenylene group “means that at least one of the substituents R, R ', and R" is a substituent other than hydrogen, and R and R' are bonded to each other to form a carbon It includes the case of forming a compound by spying together.
  • aryl group and “arylene group” have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto.
  • the aryl group or arylene group in the present invention includes monocyclic, ring conjugate, conjugated ring system, spiro compound and the like.
  • heterocyclic group includes not only aromatic rings, such as “heteroaryl groups” or “heteroarylene groups,” but also non-aromatic rings, and unless otherwise specified, each carbon number includes one or more heteroatoms. It means a ring of 2 to 60, but is not limited thereto.
  • heteroatom refers to N, O, S, P or Si unless otherwise indicated, and heterocyclic groups are monocyclic, ring conjugates, conjugated multiple ring systems, spies, including heteroatoms. Means a compound or the like.
  • Heterocyclic groups may also include rings comprising SO 2 in place of the carbon forming the ring.
  • a “heterocyclic group” includes the following compounds.
  • ring includes monocyclic and polycyclic rings, includes hydrocarbon rings as well as heterocycles including at least one heteroatom, and includes aromatic and nonaromatic rings.
  • polycyclic includes ring assemblies, fused multiple ring systems and spiro compounds, such as biphenyl, terphenyl, and the like, including aromatics as well as nonaromatics, hydrocarbons
  • the ring as well includes heterocycles comprising at least one heteroatom.
  • ring assemblies means that two or more ring systems (single or conjugated ring systems) are directly connected to each other through a single bond or a double bond and directly between such rings. It means that the number of linkages is one less than the total number of ring systems in this compound. Ring aggregates may have the same or different ring systems directly connected to each other via a single bond or a double bond.
  • conjugated multiple ring systems refers to fused ring forms that share at least two atoms, including the ring systems of two or more hydrocarbons joined together and at least one heteroatom. And heterocyclic systems having at least one conjugated form. These conjugated several ring systems can be aromatic rings, heteroaromatic rings, aliphatic rings or combinations of these rings.
  • spiro compound has a "spiro union", and a spiro linkage means a linkage formed by two rings sharing one atom only.
  • atoms shared by the two rings are called spiro atoms, and according to the number of spiro atoms in a compound, they are respectively referred to as 'monospyro-', 'diespyro-' and 'trispyro-' It is called a compound.
  • an arylalkoxy group means an alkoxy group substituted with an aryl group
  • an alkoxycarbonyl group means a carbonyl group substituted with an alkoxy group
  • an alkenyl group substituted with an arylcarbonyl group is used herein.
  • the arylcarbonyl group is a carbonyl group substituted with an aryl group.
  • substituted in the term “substituted or unsubstituted” is deuterium, halogen, amino group, nitrile group, nitro group, C1-C20 alkyl group, C1-C20 alkoxy group , C1-C20 alkylamine group, C1-C20 alkylthiophene group, C6-C20 arylthiophene group, C2-C20 alkenyl group, C2-C20 alkynyl group, C3-C20 cycloalkyl group, C6- C20 aryl group, deuterium substituted C6-C20 aryl group, C8-C20 arylalkenyl group, silane group, boron group, germanium group, and at least one selected from the group consisting of O, N, S, Si and P It means that it is substituted with one or more substituents selected from the group consisting of C2-C20 heterocyclic group containing a
  • the substituent R1 when a is an integer of 0, the substituent R1 is absent, and when a is an integer of 1, one substituent R 1 is bonded to any one of carbons forming the benzene ring, and when a is an integer of 2 or 3, respectively.
  • R 1 may be the same or different from each other, and when a is an integer from 4 to 6, is bonded to the carbon of the benzene ring in a similar manner, while the indication of hydrogen bonded to the carbon forming the benzene ring Omit.
  • FIG. 1 is an exemplary view of an organic electric device according to an embodiment of the present invention.
  • the organic electric device 100 includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110.
  • the first electrode 120 may be an anode (anode)
  • the second electrode 180 may be a cathode (cathode)
  • the first electrode may be a cathode and the second electrode may be an anode.
  • the organic layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 on the first electrode 120 in sequence.
  • at least one of these layers may be omitted, or may further include a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, a buffer layer 141, and the like.
  • the electron transport layer 160 may serve as a hole blocking layer. You could do it.
  • the organic electric device according to the present invention may further include a protective layer or a light efficiency improving layer (Capping layer) formed on one surface of the at least one surface of the first electrode and the second electrode opposite to the organic material layer.
  • a protective layer or a light efficiency improving layer Capping layer
  • Compound according to the present invention applied to the organic layer is a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, an electron injection layer 170, a light emitting layer 150, light efficiency improvement layer, light emitting auxiliary layer, etc. It can be used as a material. In one example, the compound of the present invention may be used as the light emitting auxiliary layer 151 and / or the light emitting layer 150 material.
  • the band gap, electrical characteristics, interface characteristics, etc. may vary depending on which substituents are bonded at which positions, so the selection of the cores and the combination of sub substituents bonded thereto are very important. Long life and high efficiency can be achieved at the same time when an optimal combination of energy level and T1 value and intrinsic properties (mobility, interfacial properties, etc.) of each organic material layer is achieved.
  • a light emitting auxiliary layer between the hole transport layer and the light emitting layer, and correspond to each light emitting layer (R, G, B). Therefore, it is necessary to form different emission auxiliary layers.
  • the light emitting auxiliary layer it is very difficult to infer the characteristics of the organic material layer used even if a similar core is used, since the correlation between the hole transport layer and the light emitting layer (host) should be understood.
  • the light emitting layer and / or the light emitting auxiliary layer using the compound according to the formula (1) of the present invention by optimizing the energy level (level) and T1 value, the intrinsic properties (mobility, interfacial properties, etc.) between the organic layer
  • the lifetime and efficiency of the organic electric element can be improved at the same time.
  • the organic electroluminescent device may be manufactured using various deposition methods. It may be manufactured using a deposition method such as PVD or CVD.
  • the anode 120 is formed by depositing a metal or conductive metal oxide or an alloy thereof on a substrate, and the hole injection layer 130 thereon.
  • an organic material layer including a hole transport layer 140, a light emitting layer 150, an electron transport layer 160 and an electron injection layer 170, and then depositing a material that can be used as the cathode 180 thereon have.
  • an auxiliary light emitting layer 151 may be further formed between the hole transport layer 140 and the light emitting layer 150.
  • the organic layer may be formed using a variety of polymer materials, such as a solution process or a solvent process such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, a doctor blading process, It can be produced in fewer layers by a method such as a screen printing process or a thermal transfer method. Since the organic material layer according to the present invention may be formed in various ways, the scope of the present invention is not limited by the forming method.
  • the organic electric element according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • WOLED White Organic Light Emitting Device
  • Various structures for white organic light emitting devices mainly used as backlight devices have been proposed and patented.
  • a side-by-side method in which R (Red), G (Green), and B (Blue) light emitting parts are mutually planarized, and a stacking method in which R, G, and B light emitting layers are stacked up and down.
  • CCM color conversion material
  • the organic electroluminescent device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white illumination device.
  • OLED organic electroluminescent device
  • OPC organic photoconductor
  • organic TFT organic transistor
  • Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including a control unit for controlling the display device.
  • the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.
  • the compound according to one aspect of the present invention is represented by the following formula (1).
  • R 1 , R 2 and R 3 are integers of 0-4, n is an integer of 0-3, at least one of R 1 , R 2 and R 3 is a substituent represented by the following general formula (1-1), R 1 , R 2 or R 3 not substituted with 1-1) and R 4 in formula (1-1) are each independently deuterium; halogen; C 6 ⁇ C 60 Aryl group; Fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; C 1 ⁇ C 50 Alkyl group; C 2 ⁇ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; C 1 -C 30 alkoxyl group; C 6 -C 30 aryloxy group; And -L'-N (R a ) (R b ); (wherein L 'is a single bond;
  • Ar 1 is independently of each other C 6 ⁇ C 60 An aryl group; Fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; C 1 ⁇ C 50 Alkyl group; C 2 ⁇ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; C 1 -C 30 alkoxyl group; C 6 -C 30 aryloxy group; And -L'-N (R a ) (R b );
  • a ring is selected from the group consisting of C 6 ⁇ C 24 aryl group; C 2 ⁇ C 24 heterocyclic group.
  • aryl group, heteroaryl group, fluorenyl group, arylene group, heterocyclic group and fused ring group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; -L '-N (R a) (R b); C 1 ⁇ Import alkylthio of C 20; C 1 ⁇ alkoxy group of C 20; C 1 ⁇ alkyl group of C 20; C 2 ⁇ C 20 alkenyl group a; 2 C ⁇ alkynyl of C 20; an aryl group of C 6 - C 20 substituted with heavy hydrogen;; C 6 ⁇ C 20 aryl group, a fluorenyl group; C 2 - heterocyclic group of C 20; C of 3 ⁇ C 20 cycloalkyl
  • An alkyl group may be further substituted with one or more substituents selected from the group consisting of an arylalkyl group of C
  • the compound represented by the formula (1-1) represents a compound selected from any one of the following formulas (4) to (15).
  • X is selected from the group consisting of O, S, and in the formulas (4) to (15) R 4 , o, Ar 1 is as defined in formula (1) same.
  • the present invention provides a compound represented by the following formulas (16) to (25) to present some of the specific compounds in the compound represented by the formula (1).
  • X 1 , X 2 , X 3 and X 4 are each independently CH or N, and in Formulas (24) and (25), X 1 and X 2 Are each independently O, S, or CR'R ", and R ', R" are each independently hydrogen, an alkyl group having 1 to 50 carbon atoms; C 6 ⁇ C 60 It is selected from the group consisting of aryl groups, may be bonded to each other to form a spiro ring, a is 0 or 1 and not all 0 at the same time, in the above formula (16) to (25) R 1 , R 2 , R 3 , R 4 , m, n, o, Ar 1 are the same as defined in formula (1). ⁇
  • a specific compound provides a compound in which the compound represented by the formula (1) is represented as follows.
  • the present invention provides a compound for an organic electric device represented by Chemical Formula 1.
  • the present invention provides an organic electric device containing the compound represented by the formula (1).
  • the organic electric element includes a first electrode; Second electrode; And an organic material layer positioned between the first electrode and the second electrode.
  • the organic material layer may include a compound represented by Chemical Formula 1.
  • the method may further include a light efficiency improvement layer formed on at least one side opposite to the organic material layer on one side opposite to the organic material layer or on one side of the second electrode.
  • the organic material layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process and a roll-to-roll process,
  • the present invention also provides an organic electric device in which the organic material layer comprises the compound as a phosphorescent host material of the light emitting layer.
  • the present invention is a display device comprising the above-mentioned organic electric element; And a controller for driving the display device.
  • the organic electronic device provides an electronic device according to the present invention, wherein the organic electroluminescent device is at least one of an organic electroluminescent device, an organic solar cell, an organic photoconductor, an organic transistor, and a monochromatic or white illumination device.
  • the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.
  • the compound represented by the formula (1) according to the present invention (final product) is prepared by reacting Sub 1 with Sub 2, as shown in Scheme 1 below.
  • Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2, but is not limited thereto.
  • Sub 1-1 (1) (6.4g, 20mmol) was added to a round bottom flask, Sub 1-2 (1) (5.9g, 20mmol), Pd (PPh 3 ) 4 (0.7g, 0.6mmol), NaOH ( 2.4 g, 60 mmol), THF (60 mL), water (30 mL). Thereafter, the mixture is heated to reflux at 80 ° C to 90 ° C. When the reaction is complete, distilled water is diluted at room temperature and extracted with methylene chloride and water. The organic layer was dried over MgSO 4 , concentrated, and the resulting compound was purified by silicagel column and recrystallized to give 6.2g of the product. (Yield 76%)
  • Sub 1-1 (1) (6.4g, 20mmol) was added to a round bottom flask, and Sub 1-2 (2) (5.9g, 20mmol) was obtained in the same manner as Sub 1 (1). (Yield 74%)
  • Sub 1-1 (3) (7.9g, 20mmol) was added to a round bottom flask, and Sub 1-2 (2) (5.9g, 20mmol) was obtained in the same manner as Sub 1 (1). (Yield 75%)
  • Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 3, but is not limited thereto.
  • Sub 2-1 (1) (6.4g, 20mmol) was added to a round bottom flask, Sub 1-2 (1) (5.9g, 20mmol), Pd (PPh 3 ) 4 (0.7g, 0.6mmol), NaOH ( 2.4 g, 60 mmol), THF (60 mL), water (30 mL). Thereafter, the mixture is heated to reflux at 80 ° C to 90 ° C. When the reaction is complete, distilled water is diluted at room temperature and extracted with methylene chloride and water. The organic layer was dried over MgSO 4 , concentrated, and the resulting compound was purified by silicagel column and recrystallized to obtain 6.3 g of the product. (Yield 78%)
  • Sub 3 is as follows, but is not limited thereto.
  • Sub 1 (1) (8.1 g, 20 mmol) was dissolved in toluene, then Sub 3-1 (5.8 g, 24 mmol) was added and Pd 2 (dba) 3 (0.5 g, 0.6 mmol), P (t-Bu) 3 (0.2 g, 2 mmol), NaO t -Bu (5.8 g, 60 mmol) and toluene (300 mL) were added, and the mixture was refluxed at 100 ° C. for 24 hours.
  • an organic light emitting device was manufactured according to a conventional method.
  • N 1- (naphthalen-2-yl) -N 4 , N 4 -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl as a hole injection layer ) -N 1 -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) membrane was vacuum deposited to form a thickness of 60 nm.
  • a light emitting layer having a thickness of 30 nm was deposited on the hole transport layer by doping 3 [tris (2-phenylpyridine) -iridium] at 95: 5 weight.
  • 3 tris (2-phenylpyridine) -iridium
  • BAlq hole blocking layer
  • BAlq 3 Tris (8-quinolinol) aluminum
  • LiF an alkali metal halide
  • Al was deposited to a thickness of 150 nm to prepare an organic EL device by using the Al / LiF as a cathode.
  • the electroluminescent (EL) characteristics were measured by the PR-650 of photoresearch by applying a forward bias DC voltage to the organic electroluminescent light emitting diodes prepared in Example and Comparative Example.
  • the T95 life was measured using a life measurement instrument manufactured by McScience.
  • the following table shows the results of device fabrication and evaluation.
  • the organic electroluminescent device using the organic electroluminescent device material of the present invention as a phosphorescent host can significantly improve efficiency and driving voltage.
  • Comparative Compound B and Comparative Compound C in which carbazole is substituted for indolocarbazole in the core than Comparative Compound A, which is generally used as a host material have lower driving voltage, higher efficiency, and longer lifetime.
  • the compound of the present invention, in which carbazole is substituted in the same core as Comparative Compound B and Comparative Compound C, but certain substituents such as quinazoline, benzoquinazoline, dibenzoquinazoline, benzothienopyrimidine, or benzofuroopyrimidine are substituted in carbazole The results are shown.
  • Comparative compounds B and C in which carbazole is substituted for indolocarbazole have excellent device stability as well as electrons, resulting in better device results than Comparative Compound A.
  • Comparative compounds B and C Inventive compounds substituted with specific substituents such as quinazoline, benzoquinazoline, dibenzoquinazoline, benzothienopyrimidine or benzofuroopyrimidine have higher T1 values than Comparative Compounds B and C, resulting in a lower probability of tiplet-triplet annihilation and higher LUMO values. It can be explained that the energy balance within the lamp is improved to further increase luminous efficiency. In other words, this suggests that even if the same core, the specific substituents are introduced, the chemical properties such as the energy level of the compound is changed, and the device characteristics such as the packing density is changed, so that significantly different device properties may appear.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne un composé représenté par la formule chimique (1) ci-dessous, un élément électronique organique l'utilisant, et un appareil électronique. La présente invention peut améliorer l'efficacité d'émission de lumière, la stabilité, et la durée de vie de l'élément. [Formule chimique (1) / Formule chimique (1-1)]. Dans la formule chimique (1) ci-dessus, au moins l'un des éléments R1, R2, et R3 est nécessairement un substituant représenté par la formule chimique (1-1) ci-dessous.
PCT/KR2016/007862 2015-08-03 2016-07-19 Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et dispositif électronique comprenant celui-ci WO2017022982A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2015-0109538 2015-08-03
KR1020150109538A KR102395817B1 (ko) 2015-08-03 2015-08-03 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

Publications (1)

Publication Number Publication Date
WO2017022982A1 true WO2017022982A1 (fr) 2017-02-09

Family

ID=57943408

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2016/007862 WO2017022982A1 (fr) 2015-08-03 2016-07-19 Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et dispositif électronique comprenant celui-ci

Country Status (2)

Country Link
KR (1) KR102395817B1 (fr)
WO (1) WO2017022982A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106977520A (zh) * 2017-04-19 2017-07-25 江西冠能光电材料有限公司 一种含吲哚并咔唑有机半导体材料及其有机发光器件应用

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102366722B1 (ko) * 2017-07-25 2022-02-23 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR102585263B1 (ko) * 2018-09-03 2023-10-10 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
CN114080391A (zh) * 2019-11-22 2022-02-22 株式会社Lg化学 化合物和包含其的有机发光器件

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20120129922A (ko) * 2010-01-25 2012-11-28 메르크 파텐트 게엠베하 전자 소자용 화합물
CN104119347A (zh) * 2014-07-14 2014-10-29 烟台万润精细化工股份有限公司 一种有机电致发光二极管材料及其应用
KR20150002219A (ko) * 2013-06-28 2015-01-07 주식회사 이엘엠 유기 전기 발광 조성물 및 이를 포함하는 유기 전기 발광 소자
KR20150073064A (ko) * 2013-12-20 2015-06-30 삼성디스플레이 주식회사 유기 일렉트로루미네센스 소자용 재료 및 이를 사용한 유기 일렉트로루미네센스 소자
KR20150131564A (ko) * 2014-05-15 2015-11-25 삼성전자주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1009043A3 (fr) 1998-12-09 2002-07-03 Eastman Kodak Company Dispositif électroluminescent comprenant une couche transportant des trous d'hydrocarbures polyphényles
US6465115B2 (en) 1998-12-09 2002-10-15 Eastman Kodak Company Electroluminescent device with anthracene derivatives hole transport layer
KR102429869B1 (ko) * 2014-10-17 2022-08-05 삼성전자주식회사 유기 발광 소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20120129922A (ko) * 2010-01-25 2012-11-28 메르크 파텐트 게엠베하 전자 소자용 화합물
KR20150002219A (ko) * 2013-06-28 2015-01-07 주식회사 이엘엠 유기 전기 발광 조성물 및 이를 포함하는 유기 전기 발광 소자
KR20150073064A (ko) * 2013-12-20 2015-06-30 삼성디스플레이 주식회사 유기 일렉트로루미네센스 소자용 재료 및 이를 사용한 유기 일렉트로루미네센스 소자
KR20150131564A (ko) * 2014-05-15 2015-11-25 삼성전자주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자
CN104119347A (zh) * 2014-07-14 2014-10-29 烟台万润精细化工股份有限公司 一种有机电致发光二极管材料及其应用

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106977520A (zh) * 2017-04-19 2017-07-25 江西冠能光电材料有限公司 一种含吲哚并咔唑有机半导体材料及其有机发光器件应用

Also Published As

Publication number Publication date
KR102395817B1 (ko) 2022-05-09
KR20170016135A (ko) 2017-02-13

Similar Documents

Publication Publication Date Title
WO2020226298A1 (fr) Élément électronique organique comprenant un composé pour élément électronique organique, et dispositif électronique associé
WO2019124902A1 (fr) Élément électronique organique utilisant un composé d'élément électronique organique et dispositif électronique associé
WO2017105078A1 (fr) Composé pour élément électrique organique, élément électrique organique contenant ledit composé, et dispositif électronique associé
WO2016003225A2 (fr) Composé pour élément électronique organique, élément électronique organique utilisant ledit composé et dispositif électronique comprenant ledit composé
WO2016140497A2 (fr) Composé pour dispositif électrique organique, dispositif électrique organique l'utilisant, et dispositif électronique associé
WO2018016786A1 (fr) Composé pour dispositif électronique organique, dispositif électronique organique l'utilisant et appareil électronique associé
WO2015041416A1 (fr) Élément électrique organique utilisant des composés pour un élément électrique organique et dispositif électronique pour ce dernier
WO2016056757A2 (fr) Composé pour élément électro-organique, élément électro-organique et appareil électronique l'utilisant
WO2017052129A1 (fr) Nouveau composé pour dispositif électrique organique, dispositif électrique organique l'utilisant et dispositif électronique le comprenant
WO2016013816A1 (fr) Élément électrique organique faisant appel à un composé pour élément électrique organique, et dispositif électronique associé
WO2014058183A1 (fr) Composé pour dispositif électronique organique, dispositif électronique organique l'utilisant et appareil électronique dudit dispositif électronique organique
WO2015056965A1 (fr) Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et dispositif électronique associé
WO2018056649A1 (fr) Composé pour élément électronique organique, élément électronique organique l'utilisant et dispositif électronique associé
WO2015080404A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique correspondant
WO2015088183A1 (fr) Composé pour élément organique électrique, élément organique électrique l'utilisant et dispositif électronique correspondant
WO2019093666A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique
WO2020085797A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique associé
WO2017052099A1 (fr) Composé pour dispositif électronique organique, dispositif électronique organique l'utilisant et dispositif électronique associé
WO2020149710A1 (fr) Composé pour élément électronique organique, élément électronique organique l'utilisant et dispositif électronique associé
WO2016153198A1 (fr) Composé pour dispositif électronique organique, dispositif électronique organique l'utilisant et appareil électronique associé
WO2016013817A2 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique correspondant
WO2019022435A1 (fr) Composé pour dispositif électronique organique, dispositif électronique organique l'utilisant et appareil électronique associé
WO2017014460A1 (fr) Composé pour élément électronique organique, élément électronique organique utilisant ce composé et dispositif électronique associé
WO2018169261A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique associé
WO2019031833A1 (fr) Composé pour élément électronique organique, élément électronique organique utilisant ce composé, et dispositif électronique

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 16833218

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 16833218

Country of ref document: EP

Kind code of ref document: A1